Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 1, Pages 17-46Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2020246
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Funding
- NSF [CHE-0847061]
- Eli Lilly
- NSERC of Canada
- Bristol-Myers Squibb
- UC Irvine UROP
- Allergan
- Amgen
- AstraZeneca
- NSF CRIF [CIE-0840513]
- Direct For Mathematical & Physical Scien [0847061] Funding Source: National Science Foundation
- Division Of Chemistry [0847061] Funding Source: National Science Foundation
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A full account of the development of the base-mediated intramolecular Diets-Alder cycloadditions of tryptamine-derived Zincke aldehydes is described. This important complexity-generating transformation provides the tetracyclic core of many indole monoterpene alkaloids in only three steps from commercially available starting materials and played a key role in short syntheses of norfluorocurarine (five steps), dehydrodesacetylretuline (six steps), valparicine (seven steps), and strychnine (six steps). Reasonable mechanistic possibilities for this reaction, a surprisingly facile dimerization of the products, and an unexpected cycloreversion to regenerate Zincke aldehydes under specific conditions are also discussed.
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